BikesEven the most confident women I know struggle with the decision to resign from their job and move on to something else. Lately, I’ve seen many women in my life jumping ship. They have looked deeply into what makes them happy and come face-to-face with the future staring back. The road they take isn’t without some nerve-racking potholes: resigning from secure jobs, ditching stable clients, taking (gasp) less money, and quitting without having a new gig lined up. They attend workshops on how to freeze eggs, revisit family planning, and blaze new paths against the advice of significant others.

But is there some secret guiding them? Not at all. Like many women making a drastic change in their lives, they struggle with the unknown.

Few of us make these decisions lightly. Some of the things you may weigh before making the change could include factoring in what you will lose – or at least, what you think you may lose. Here are five questions you should ask yourself before pulling the trigger on a life-altering career decision.

1. Why Change Your Life and Start a New Career?

Why not be happy? You’ve been in the same position long enough to see the company change, and you are no longer satisfied with your job. This is what tipped the scale for my friends:

- Your role changed: A friend of mine was bumped to another section. One minute, she’s leading a multimillion-dollar growth initiative at a company worth $40 billion; the next, she’s assigned to the tedium of the corporate strategy unit because her company lacked a culture of experimentation. She knew her value and quickly started the job search, receiving offers from both Twitter and Facebook. She is now enjoying her new role as a product manager at the latter.

- You deserve career advancement: Another one of my friends felt that her small team did not allow for growth. She wrestled with moving out of EdTech, and only after months of soul-searching and career coaching did she find a perfect fit as an interactive producer for an advertising agency.

- You’re seeking a challenge: One of my friends reached the top of the ranks and was running the place like a champ, but she became bored with the minutia. She craved something more creative. Rather than taking a similar type of job with Pandora, she opted for a pay cut and now serves as a project manager for a highly-regarded agency with clients like Netflix, Amazon, and Google.

- You’re in the wrong industry: Two friends, after years of law school and big firm work, found themselves in what was (for them) the wrong career. One went directly into nursing school, while the other lived off of her savings, taking time off to find the “right” job – and is now director of development for a solar energy company.

Camera- You need a better environmental fit: A different friend’s favorite boss left, leaving a management void in an already negative company culture. She left to spend a year at home with her two young kids before landing a program management position at an innovative technology company.

The result? I can assure you that none of them have ever looked back.

2. What Matters Most in Your Career?

Here are some common answers I’ve seen:

- Flexibility: You like the prospect of having more time to travel or work on personal projects.

- Learning: You’re looking for new challenges.

- Ownership: You want work that matches your need for a sense of fulfillment.

We want money, yes, but we also want jobs that suit our lifestyles – which could mean fewer hours, nicer people, more freedom of choice, childcare on site, and anything else that will make us happy.

Other things to considering include: Do you have the support of your significant other? Are you planning on conceiving soon? Adopting? Freezing eggs? Remaining childless? Considering what all of these things might mean to you and your career, taking stock of them can contribute to your decision. We tend to feel more at ease when our personal and professional lives exist together in harmony.

3. What Am I Afraid Of?

Many are afraid of leaving a career they’re good at, the short-term financial insecurity, the lost camaraderie of current workplace friends, or having to start over at the bottom. Rest assured, however, that virtually all of these fears are experienced by confident women who make successful career transitions.

One such woman, Gazelle Javantash, says, “Considering how much I spent on my education and a master’s degree, I told myself I couldn’t start at entry level with this much debt. So I hired a career coach.”

Through this process, Gazelle moved from education into the private tech sector. Her coach helped her to weigh all of these questions and identify the role she wanted her career to play in her life.

4. What Do I Have to Gain?

The answer to this question is different for everyone. Maybe your desire for a career change comes from career and personal satisfaction, or you anticipate this new role giving you more free time, or this new direction provides the financial boost to start saving for retirement or a home. In any case, confident women who make career transitions know that doing so always requires a leap of faith.

5. How Do I Ultimately Decide What to Do?

moonHow did all of these powerful women in my life come to the decision to pick up their padfolios and hit the road? We talked to our partners, and we talked to each other. Most of us, in fact, had been thinking about jumping ship for months. We would casually mention the idea in passing – over a glass of wine, in the pool, on an airplane, or while hiking up a mountain. We listened to one another, helped each other weigh all of the pros and cons, asked ourselves what we had “to lose,” and then finally delivered our recommendations to one another.

Ultimately, no one else can make the decision for you. Everyone will give you advice and try to help, but in the end, you are the only one who truly knows what’s right for you. In your heart, you will know when it’s time for a change.

The final decision will not be easy. It’s never easy to choose the road less traveled and dive into something new. While change is scary, you know in your gut when it’s necessary.

Once you do decide to take that first step, don’t look back. We did it, and you can, too.


This article originally appeared on BusinessCollective.

Heather McGough is cofounder, with Eric Ries and Melissa Moore, of Lean Startup Company. For five years, she has been providing education, tools, and partnerships to entrepreneurs and corporate innovators, empowering them to overcome challenges in building new companies and products. Heather develops new ways to support the global community of aspiring and existing Lean Startup practitioners for companies both large and small in any sector. She has also formed the event production firm Urbanity Events and startup Adoptful. 

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